In my experience it is common and customary for the landlord or builder to provide TIA, tenant improvement allowance, to the tenant to assist if not cover the majority of the internal buildout. 

I wouldn't imaging the state where the entity is registered makes a big difference for most buying and selling purposes as long as you can provide all of the required documents for title purposes.

Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax?

We currently have a DSCR loan on this property and paid $180k for it. 

Quote from @Jaycee Greene: Hey Jaycee, we currently lend on several loan types: Fix & Flip up to 90% LTP, BRRRR, New Construction, Bridge Loans, & Multi-Family.For myself personally, I'm looking in the Orlando, Philadelphia, and Southern NJ markets, 1-4 units.

You can finance it with an FHA loan (3.5% down) or a conventional loan (5% down) if you plan to live in the property.

Use a home equity loan (fixed debt) instead of a HELOC (variable equity) and build an additional unit you can rent out in your own backyard.

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House hacking a 2-4 unit property with FHA (3.5% down) or Conventional (5% down) can be a smart way to start, while DSCR loans or partnerships can help if you need alternative financing.

Conventional loan with a 20% down payment.